Literature DB >> 24687140

A new approach towards the synthesis of pseudaminic acid analogues.

Matthew Zunk1, James Williams, James Carter, Milton J Kiefel.   

Abstract

The pseudaminic acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids that are essential components of bacterial polysaccharides and glycoproteins. This paper describes our approach towards the synthesis of analogues of pseudaminic acid, and involves the efficient introduction of the requisite nitrogen functionalities from a readily available precursor.

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Year:  2014        PMID： 24687140     DOI： 10.1039/c3ob42491j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  9 in total

1.  Use of Phenols as Nucleophiles in the Zbiral Oxidative Deamination of N-Acetyl Neuraminic Acid: Isolation and Characterization of Tricyclic 3-Keto-2-deoxy-nonulosonic Acid (KDN) Derivatives via an Intermediate Vinyl Diazonium Ion.

Authors:  Mohammed Hawsawi; Anura Wickramasinghe; David Crich
Journal:  J Org Chem       Date:  2019-10-29       Impact factor: 4.354

2.  Stereoselective Synthesis of 5-epi-α-Sialosides Related to the Pseudaminic Acid Glycosides. Reassessment of the Stereoselectivity of the 5-Azido-5-deacetamidosialyl Thioglycosides and Use of Triflate as Nucleophile in the Zbiral Deamination of Sialic Acids.

Authors:  Bibek Dhakal; Szymon Buda; David Crich
Journal:  J Org Chem       Date:  2016-11-10       Impact factor: 4.354

3.  Syntheses of Legionaminic Acid, Pseudaminic Acid, Acetaminic Acid, 8-epi-Acetaminic Acid, and 8-epi-Legionaminic Acid Glycosyl Donors from N-Acetylneuraminic Acid by Side Chain Exchange.

Authors:  Sameera Siyabalapitiya Arachchige; David Crich
Journal:  Org Lett       Date:  2022-04-14       Impact factor: 6.072

4.  Oxidative deamination of amino sugars: recent advances.

Authors:  Vikram A Sarpe; David Crich
Journal:  Carbohydr Chem       Date:  2001-03-06

5.  Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.

Authors:  Bibek Dhakal; David Crich
Journal:  J Am Chem Soc       Date:  2018-10-25       Impact factor: 15.419

6.  Oxidative Deamination of N-Acetyl Neuraminic Acid: Substituent Effects and Mechanism.

Authors:  Szymon Buda; David Crich
Journal:  J Am Chem Soc       Date:  2016-01-15       Impact factor: 15.419

7.  Use of hydroxylamines, hydroxamic acids, oximes and amines as nucleophiles in the Zbiral oxidative deamination of N-acetyl neuraminic acid. Isolation and characterization of novel mono- and disubstitution products.

Authors:  Mohammed Hawsawi; Michael G Pirrone; Anura Wickramasinghe; David Crich
Journal:  Carbohydr Res       Date:  2020-01-25       Impact factor: 2.104

8.  An efficient and scalable synthesis of 2,4-di-N-acetyl-l-altrose (l-2,4-Alt-diNAc).

Authors:  Anna Niedzwiecka; Carita Sequeira; Ping Zhang; Chang-Chun Ling
Journal:  RSC Adv       Date:  2021-03-19       Impact factor: 3.361

9.  A new approach to the synthesis of legionaminic acid analogues.

Authors:  James R Carter; Milton J Kiefel
Journal:  RSC Adv       Date:  2018-10-19       Impact factor: 4.036
  9 in total

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